Total synthesis of (±)-debromoflustramine B and E and (±)-debromoflustramide B based on one-pot intramolecular Ullmann coupling and Claisen rearrangement

Tetrahedron Letters

Volumn 48, Issue 10, 2007, Pages 1805-1808

  Miyamoto, Hiroshi ^a   Okawa, Yoichiro ^a   Nakazaki, Atsuo ^a   Kobayashi, Susumu ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Claisen rearrangement; One pot reaction; Oxindoles; Pyrrolidinoindoline alkaloids; Total synthesis; Ullmann coupling

Indexed keywords

DEBROMOFLUSTRAMIDE B; DEBROMOFLUSTRAMINE B; DEBROMOFLUSTRAMINE E; INDOLE DERIVATIVE; NATURAL PRODUCT; OXINDOLE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CLAISEN REARRANGEMENT; DRUG STRUCTURE; DRUG SYNTHESIS; STRUCTURE ANALYSIS; ULLMANN COUPLING;

EID: 33846804205     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.01.002     Document Type: Article

References (26)

1. For reviews, see:. Anthoni U., Christophersen C., and Nielsen P.H. In: Pelletier S.W. (Ed). Alkaloids: Chemical and Biological Perspectives Vol. 13 (1999), Wiley, New York 163-236
2. Wright J.L.C. J. Nat. Prod. 47 (1984) 893-895
3. Laycock M.V., Wright J.L.C., Findlay J.A., and Patil A.D. Can. J. Chem. 64 (1986) 1312-1316
4. Holst P.B., Anthoni U., Christophersen C., and Nielsen P.H. J. Nat. Prod. 57 (1994) 997-1000
5. Peters L., König G.M., Terlau H., and Wright A.D. J. Nat. Prod. 65 (2002) 1633-1637
6. Carlé J.S., and Christophersen C. J. Am. Chem. Soc. 101 (1979) 4012-4013
7. Carlé J.S., and Christophersen C. J. Org. Chem. 45 (1980) 1586-1589
8. Sjöblom T., Bohlin L., and Christophersen C. Acta Pharm. Suec. 20 (1983) 415-418
9. Smith B.P., Tyler M.J., Kaneko T., Garraffo H.M., Spande T.F., and Daly J.W. J. Nat. Prod. 65 (2002) 439-447
10. Hodgson J.W., Mitchell M.O., Thomas M.L., and Waters K.F. Bioorg. Med. Chem. Lett. 5 (1995) 2527-2528
11. Dix A.V., Meseck C.M., Lowe A.J., and Mitchell M.O. Bioorg. Med. Chem. Lett. 16 (2006) 2522-2524
12. For synthesis of enantiomerically pure pyrrolidinoindolines, see:. Kawasaki T., Shinada M., Kamimura D., Ohzono M., and Ogawa A. Chem. Commun. (2006) 420-422
13. Bruncko M., Crich D., and Samy R. J. Org. Chem. 59 (1994) 5543-5549
14. Morales-Ríos M.S., Rivera-Becerril E., and Joseph-Nathan P. Tetrahedron: Asymmetry 16 (2005) 2493-2499
15. Cardoso A.S., Srinivasan N., Lobo A.M., and Prabhakar S. Tetrahedron Lett. 42 (2001) 6663-6666
16. For racemic synthesis, see:. López-Alvarado P., Caballero E., Avendaño C., and Menéndez J.C. Org. Lett. 8 (2006) 4303-4306
17. Tan G.H., Zhu X., and Ganesan A. Org. Lett. 5 (2003) 1801-1803
18. Morales-Ríos M.S., Suárez-Castillo O.R., Trujillo-Serrato J.J., and Joseph-Nathan P. J. Org. Chem. 66 (2001) 1186-1192
19. Morales-Ríos M.S., Suárez-Castillo O.R., and Joseph-Nathan P. Tetrahedron 58 (2002) 1479-1484
20. Somei M., Yamada F., Izumi T., and Nakajou M. Heterocycles 45 (1997) 2327-2330
21. Jensen J., Anthoni U., Christophersen C., and Nielsen P.H. Acta Chem. Scand. 49 (1995) 68-71
22. Mitchell M.O., and Dorroh P. Tetrahedron Lett. 32 (1991) 7641-7642
23. Miyamoto H., Okawa Y., Nakazaki A., and Kobayashi S. Angew. Chem., Int. Ed. 45 (2006) 2274-2277
24. Bergman J., and Venemalm L. J. Org. Chem. 57 (1992) 2495-2497
25. Yadav J.S., Abraham S., Reddy B.V.S., and Sabitha G. Synthesis (2001) 2165-2169
26. Huang A., Kodanko J.J., and Overman L.E. J. Am. Chem. Soc. 126 (2004) 14043-14053